Biosynthetic investigations of the V-type ATPase inhibitors bafilomycin A1, B1 and concanamycin A.

Tim Schuhmann, Stephanie Grond

Index: J. Antibiot. 57(10) , 655-61, (2004)

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Abstract

The plecomacrolides bafilomycin A1 and B1 (1, 2) and concanamycin A (3), produced by different Streptomyces species, show a unique macrolactone structure with characteristic side chains and exhibit striking biological activities including distinct V-type ATPase inhibition. The biosynthesis of 1 and 2 has been established by feeding experiments with 13C-labelled precursors. Both, bafilomycin (1, 2) and concanamycin (3) feature an "unusual C2 chain extension unit" of as yet unknown origin which was addressed by feeding labelled 2-hydroxy- and 2-methoxymalonyl-derivatives.